Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016946/wk6050sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016946/wk6050Isup2.hkl |
CCDC reference: 277801
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.054
- wR factor = 0.130
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 2
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C8 - C10 ... 1.44 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).
C24H19N3O2 | F(000) = 1600 |
Mr = 381.42 | Dx = 1.272 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 4326 reflections |
a = 9.801 (3) Å | θ = 2.6–27.0° |
b = 15.549 (4) Å | µ = 0.08 mm−1 |
c = 26.142 (7) Å | T = 273 K |
V = 3984.1 (19) Å3 | Block, colorless |
Z = 8 | 0.48 × 0.37 × 0.32 mm |
Bruker SMART CCD 1K area-detector diffractometer | 2563 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.041 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 27.1°, θmin = 2.6° |
Tmin = 0.961, Tmax = 0.974 | h = −12→12 |
17659 measured reflections | k = −19→19 |
4326 independent reflections | l = −33→18 |
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Only H-atom displacement parameters refined |
R[F2 > 2σ(F2)] = 0.054 | w = 1/[σ2(Fo2) + (0.0634P)2 + 2.2522P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.130 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.38 e Å−3 |
4326 reflections | Δρmin = −0.56 e Å−3 |
261 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | −0.1756 (2) | 0.30445 (13) | 0.00221 (6) | 0.0669 (6) | |
O2A | 0.5881 (4) | 0.4511 (3) | 0.1531 (2) | 0.0535 (16)* | 0.453 (10) |
O2B | 0.5977 (3) | 0.4568 (2) | 0.1741 (2) | 0.0599 (14)* | 0.547 (10) |
N1 | −0.03100 (18) | 0.16509 (12) | 0.22640 (6) | 0.0365 (4) | |
H1A | −0.1083 | 0.1414 | 0.2198 | 0.044* | |
N2 | 0.15676 (18) | 0.19979 (12) | 0.26803 (6) | 0.0375 (4) | |
N3 | −0.2246 (3) | −0.02281 (18) | 0.48686 (10) | 0.0870 (9) | |
C1 | 0.0502 (2) | 0.12506 (16) | 0.36298 (8) | 0.0426 (6) | |
H1 | 0.1312 | 0.1561 | 0.3647 | 0.051* | |
C2 | −0.0146 (2) | 0.11409 (14) | 0.31590 (7) | 0.0342 (5) | |
C3 | 0.0395 (2) | 0.15785 (14) | 0.27065 (8) | 0.0344 (5) | |
C4 | 0.1590 (2) | 0.23811 (14) | 0.22041 (8) | 0.0357 (5) | |
C5 | 0.0422 (2) | 0.21675 (14) | 0.19388 (8) | 0.0343 (5) | |
C6 | −0.1337 (2) | 0.06622 (15) | 0.31409 (9) | 0.0434 (6) | |
H6 | −0.1770 | 0.0572 | 0.2829 | 0.052* | |
C7 | −0.1890 (3) | 0.03175 (16) | 0.35818 (9) | 0.0477 (6) | |
H7 | −0.2695 | 0.0003 | 0.3565 | 0.057* | |
C8 | −0.1246 (3) | 0.04394 (15) | 0.40491 (8) | 0.0436 (6) | |
C9 | −0.0042 (3) | 0.09058 (16) | 0.40698 (9) | 0.0467 (6) | |
H9 | 0.0398 | 0.0986 | 0.4381 | 0.056* | |
C10 | −0.1822 (3) | 0.00799 (18) | 0.45080 (10) | 0.0578 (7) | |
C11 | 0.2726 (2) | 0.29387 (15) | 0.20442 (8) | 0.0386 (5) | |
C12 | 0.3309 (3) | 0.35160 (17) | 0.23854 (10) | 0.0514 (6) | |
H12 | 0.2973 | 0.3551 | 0.2718 | 0.062* | |
C13 | 0.4376 (3) | 0.40379 (18) | 0.22395 (12) | 0.0629 (8) | |
H13 | 0.4748 | 0.4419 | 0.2476 | 0.076* | |
C14 | 0.4902 (2) | 0.40073 (16) | 0.17515 (13) | 0.0615 (8) | |
C15 | 0.4324 (3) | 0.34407 (18) | 0.14061 (11) | 0.0585 (8) | |
H15 | 0.4656 | 0.3414 | 0.1073 | 0.070* | |
C16 | 0.3252 (2) | 0.29106 (16) | 0.15525 (10) | 0.0456 (6) | |
H16 | 0.2880 | 0.2530 | 0.1316 | 0.055* | |
C17 | −0.0113 (2) | 0.23867 (14) | 0.14317 (8) | 0.0353 (5) | |
C18 | −0.0015 (2) | 0.32100 (15) | 0.12327 (8) | 0.0412 (5) | |
H18 | 0.0428 | 0.3636 | 0.1419 | 0.049* | |
C19 | −0.0565 (2) | 0.34054 (16) | 0.07613 (9) | 0.0452 (6) | |
H19 | −0.0481 | 0.3959 | 0.0631 | 0.054* | |
C20 | −0.1239 (2) | 0.27831 (17) | 0.04820 (8) | 0.0441 (6) | |
C21 | −0.1337 (3) | 0.19588 (17) | 0.06687 (8) | 0.0482 (6) | |
H21 | −0.1776 | 0.1534 | 0.0480 | 0.058* | |
C22 | −0.0774 (2) | 0.17702 (16) | 0.11402 (8) | 0.0435 (6) | |
H22 | −0.0840 | 0.1212 | 0.1266 | 0.052* | |
C23 | −0.2822 (4) | 0.2570 (2) | −0.01908 (11) | 0.0846 (11) | |
H23A | −0.3084 | 0.2821 | −0.0511 | 0.127* | |
H23B | −0.3587 | 0.2573 | 0.0038 | 0.127* | |
H23C | −0.2527 | 0.1988 | −0.0246 | 0.127* | |
C24A | 0.6389 (7) | 0.4476 (4) | 0.1032 (2) | 0.060 (2)* | 0.453 (10) |
H24A | 0.7100 | 0.4896 | 0.0993 | 0.090* | 0.453 (10) |
H24B | 0.5667 | 0.4596 | 0.0795 | 0.090* | 0.453 (10) |
H24C | 0.6750 | 0.3913 | 0.0967 | 0.090* | 0.453 (10) |
C24B | 0.6769 (6) | 0.4419 (4) | 0.1306 (3) | 0.078 (2)* | 0.547 (10) |
H24D | 0.7534 | 0.4805 | 0.1305 | 0.117* | 0.547 (10) |
H24E | 0.6227 | 0.4514 | 0.1006 | 0.117* | 0.547 (10) |
H24F | 0.7091 | 0.3836 | 0.1309 | 0.117* | 0.547 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0731 (13) | 0.0811 (14) | 0.0465 (10) | −0.0207 (11) | −0.0216 (9) | 0.0206 (10) |
N1 | 0.0314 (9) | 0.0441 (11) | 0.0341 (10) | −0.0072 (8) | −0.0013 (7) | −0.0002 (8) |
N2 | 0.0312 (10) | 0.0452 (11) | 0.0362 (10) | −0.0021 (9) | −0.0015 (8) | 0.0025 (8) |
N3 | 0.123 (3) | 0.0772 (19) | 0.0605 (16) | −0.0118 (17) | 0.0285 (16) | 0.0173 (14) |
C1 | 0.0370 (12) | 0.0502 (14) | 0.0406 (12) | −0.0026 (11) | −0.0040 (10) | 0.0034 (11) |
C2 | 0.0306 (11) | 0.0363 (12) | 0.0357 (11) | 0.0029 (10) | 0.0005 (9) | 0.0023 (9) |
C3 | 0.0312 (11) | 0.0390 (12) | 0.0330 (11) | 0.0004 (10) | −0.0004 (9) | −0.0003 (9) |
C4 | 0.0319 (11) | 0.0400 (13) | 0.0350 (11) | −0.0009 (10) | 0.0026 (9) | −0.0004 (9) |
C5 | 0.0313 (11) | 0.0388 (12) | 0.0330 (11) | −0.0023 (10) | 0.0031 (9) | −0.0008 (9) |
C6 | 0.0443 (14) | 0.0446 (14) | 0.0412 (13) | −0.0043 (11) | −0.0032 (10) | 0.0023 (10) |
C7 | 0.0472 (14) | 0.0429 (14) | 0.0531 (15) | −0.0111 (12) | 0.0033 (11) | 0.0063 (11) |
C8 | 0.0549 (15) | 0.0368 (13) | 0.0393 (12) | 0.0024 (12) | 0.0084 (11) | 0.0053 (10) |
C9 | 0.0529 (15) | 0.0514 (15) | 0.0358 (12) | 0.0000 (13) | −0.0041 (11) | 0.0038 (11) |
C10 | 0.0739 (19) | 0.0497 (16) | 0.0499 (15) | −0.0016 (15) | 0.0118 (13) | 0.0092 (13) |
C11 | 0.0295 (11) | 0.0409 (13) | 0.0455 (13) | 0.0006 (10) | −0.0027 (9) | 0.0063 (10) |
C12 | 0.0471 (14) | 0.0529 (16) | 0.0543 (15) | −0.0068 (13) | −0.0078 (12) | 0.0037 (12) |
C13 | 0.0485 (16) | 0.0516 (17) | 0.089 (2) | −0.0145 (14) | −0.0167 (15) | 0.0069 (15) |
C14 | 0.0297 (13) | 0.0402 (15) | 0.115 (3) | −0.0059 (12) | 0.0046 (15) | 0.0234 (16) |
C15 | 0.0431 (14) | 0.0549 (17) | 0.0774 (19) | 0.0078 (14) | 0.0225 (13) | 0.0215 (14) |
C16 | 0.0369 (13) | 0.0468 (14) | 0.0531 (14) | 0.0026 (11) | 0.0057 (11) | 0.0059 (11) |
C17 | 0.0312 (11) | 0.0434 (13) | 0.0313 (11) | −0.0017 (10) | 0.0018 (9) | −0.0004 (9) |
C18 | 0.0389 (12) | 0.0427 (13) | 0.0419 (12) | −0.0048 (11) | −0.0024 (10) | −0.0030 (10) |
C19 | 0.0457 (13) | 0.0436 (14) | 0.0462 (13) | −0.0021 (12) | −0.0017 (11) | 0.0087 (11) |
C20 | 0.0416 (13) | 0.0569 (16) | 0.0337 (12) | −0.0058 (12) | −0.0014 (10) | 0.0070 (10) |
C21 | 0.0547 (15) | 0.0542 (16) | 0.0357 (12) | −0.0168 (13) | −0.0063 (11) | −0.0017 (11) |
C22 | 0.0502 (14) | 0.0429 (14) | 0.0375 (12) | −0.0103 (12) | −0.0003 (10) | 0.0046 (10) |
C23 | 0.091 (2) | 0.106 (3) | 0.0569 (18) | −0.024 (2) | −0.0336 (17) | 0.0160 (18) |
O1—C20 | 1.367 (3) | C11—C12 | 1.388 (3) |
O1—C23 | 1.395 (3) | C12—C13 | 1.378 (4) |
O2A—C14 | 1.3663 (10) | C12—H12 | 0.9300 |
O2A—C24A | 1.3961 (11) | C13—C14 | 1.377 (4) |
O2B—C14 | 1.3677 (10) | C13—H13 | 0.9300 |
O2B—C24B | 1.3966 (11) | C14—C15 | 1.383 (4) |
N1—C3 | 1.352 (2) | C15—C16 | 1.390 (3) |
N1—C5 | 1.372 (3) | C15—H15 | 0.9300 |
N1—H1A | 0.8600 | C16—H16 | 0.9300 |
N2—C3 | 1.323 (3) | C17—C22 | 1.385 (3) |
N2—C4 | 1.380 (3) | C17—C18 | 1.385 (3) |
N3—C10 | 1.136 (3) | C18—C19 | 1.379 (3) |
C1—C9 | 1.377 (3) | C18—H18 | 0.9300 |
C1—C2 | 1.395 (3) | C19—C20 | 1.381 (3) |
C1—H1 | 0.9300 | C19—H19 | 0.9300 |
C2—C6 | 1.386 (3) | C20—C21 | 1.375 (3) |
C2—C3 | 1.464 (3) | C21—C22 | 1.382 (3) |
C4—C5 | 1.380 (3) | C21—H21 | 0.9300 |
C4—C11 | 1.472 (3) | C22—H22 | 0.9300 |
C5—C17 | 1.466 (3) | C23—H23A | 0.9600 |
C6—C7 | 1.381 (3) | C23—H23B | 0.9600 |
C6—H6 | 0.9300 | C23—H23C | 0.9600 |
C7—C8 | 1.388 (3) | C24A—H24A | 0.9600 |
C7—H7 | 0.9300 | C24A—H24B | 0.9600 |
C8—C9 | 1.386 (3) | C24A—H24C | 0.9600 |
C8—C10 | 1.439 (3) | C24B—H24D | 0.9600 |
C9—H9 | 0.9300 | C24B—H24E | 0.9600 |
C11—C16 | 1.386 (3) | C24B—H24F | 0.9600 |
C20—O1—C23 | 118.1 (2) | O2A—C14—C15 | 112.1 (4) |
C14—O2A—C24A | 128.5 (5) | O2B—C14—C15 | 135.2 (3) |
C14—O2B—C24B | 109.7 (4) | C13—C14—C15 | 118.3 (2) |
C3—N1—C5 | 108.16 (17) | C14—C15—C16 | 120.5 (2) |
C3—N1—H1A | 125.9 | C14—C15—H15 | 119.7 |
C5—N1—H1A | 125.9 | C16—C15—H15 | 119.7 |
C3—N2—C4 | 105.87 (17) | C11—C16—C15 | 121.2 (3) |
C9—C1—C2 | 120.9 (2) | C11—C16—H16 | 119.4 |
C9—C1—H1 | 119.6 | C15—C16—H16 | 119.4 |
C2—C1—H1 | 119.6 | C22—C17—C18 | 117.7 (2) |
C6—C2—C1 | 118.6 (2) | C22—C17—C5 | 120.3 (2) |
C6—C2—C3 | 121.81 (19) | C18—C17—C5 | 122.0 (2) |
C1—C2—C3 | 119.4 (2) | C19—C18—C17 | 120.8 (2) |
N2—C3—N1 | 111.01 (18) | C19—C18—H18 | 119.6 |
N2—C3—C2 | 125.83 (18) | C17—C18—H18 | 119.6 |
N1—C3—C2 | 123.02 (19) | C18—C19—C20 | 120.4 (2) |
C5—C4—N2 | 109.63 (18) | C18—C19—H19 | 119.8 |
C5—C4—C11 | 128.84 (19) | C20—C19—H19 | 119.8 |
N2—C4—C11 | 121.52 (18) | O1—C20—C21 | 124.3 (2) |
N1—C5—C4 | 105.28 (18) | O1—C20—C19 | 115.8 (2) |
N1—C5—C17 | 120.63 (18) | C21—C20—C19 | 119.9 (2) |
C4—C5—C17 | 134.1 (2) | C20—C21—C22 | 119.1 (2) |
C7—C6—C2 | 120.7 (2) | C20—C21—H21 | 120.4 |
C7—C6—H6 | 119.7 | C22—C21—H21 | 120.4 |
C2—C6—H6 | 119.7 | C21—C22—C17 | 122.0 (2) |
C6—C7—C8 | 120.2 (2) | C21—C22—H22 | 119.0 |
C6—C7—H7 | 119.9 | C17—C22—H22 | 119.0 |
C8—C7—H7 | 119.9 | O1—C23—H23A | 109.5 |
C9—C8—C7 | 119.5 (2) | O1—C23—H23B | 109.5 |
C9—C8—C10 | 120.3 (2) | H23A—C23—H23B | 109.5 |
C7—C8—C10 | 120.1 (2) | O1—C23—H23C | 109.5 |
C1—C9—C8 | 120.1 (2) | H23A—C23—H23C | 109.5 |
C1—C9—H9 | 120.0 | H23B—C23—H23C | 109.5 |
C8—C9—H9 | 120.0 | O2A—C24A—H24A | 109.5 |
N3—C10—C8 | 177.5 (3) | O2A—C24A—H24B | 109.5 |
C16—C11—C12 | 117.6 (2) | H24A—C24A—H24B | 109.5 |
C16—C11—C4 | 121.8 (2) | O2A—C24A—H24C | 109.5 |
C12—C11—C4 | 120.6 (2) | H24A—C24A—H24C | 109.5 |
C13—C12—C11 | 121.0 (3) | H24B—C24A—H24C | 109.5 |
C13—C12—H12 | 119.5 | O2B—C24B—H24D | 109.5 |
C11—C12—H12 | 119.5 | O2B—C24B—H24E | 109.5 |
C14—C13—C12 | 121.4 (3) | H24D—C24B—H24E | 109.5 |
C14—C13—H13 | 119.3 | O2B—C24B—H24F | 109.5 |
C12—C13—H13 | 119.3 | H24D—C24B—H24F | 109.5 |
O2A—C14—C13 | 129.4 (4) | H24E—C24B—H24F | 109.5 |
O2B—C14—C13 | 106.5 (3) | ||
C9—C1—C2—C6 | −1.3 (3) | C11—C12—C13—C14 | 0.0 (4) |
C9—C1—C2—C3 | 174.7 (2) | C24A—O2A—C14—O2B | 162.0 (10) |
C4—N2—C3—N1 | 2.1 (2) | C24A—O2A—C14—C13 | −179.1 (5) |
C4—N2—C3—C2 | −173.7 (2) | C24A—O2A—C14—C15 | −4.3 (6) |
C5—N1—C3—N2 | −2.0 (2) | C24B—O2B—C14—O2A | −29.9 (6) |
C5—N1—C3—C2 | 173.91 (19) | C24B—O2B—C14—C13 | 165.2 (4) |
C6—C2—C3—N2 | −175.1 (2) | C24B—O2B—C14—C15 | −11.9 (6) |
C1—C2—C3—N2 | 9.1 (3) | C12—C13—C14—O2A | 175.0 (3) |
C6—C2—C3—N1 | 9.6 (3) | C12—C13—C14—O2B | −177.2 (3) |
C1—C2—C3—N1 | −166.2 (2) | C12—C13—C14—C15 | 0.5 (4) |
C3—N2—C4—C5 | −1.4 (2) | O2A—C14—C15—C16 | −176.2 (3) |
C3—N2—C4—C11 | 177.4 (2) | O2B—C14—C15—C16 | 176.1 (3) |
C3—N1—C5—C4 | 1.1 (2) | C13—C14—C15—C16 | −0.8 (4) |
C3—N1—C5—C17 | −178.0 (2) | C12—C11—C16—C15 | 0.1 (3) |
N2—C4—C5—N1 | 0.2 (2) | C4—C11—C16—C15 | 180.0 (2) |
C11—C4—C5—N1 | −178.5 (2) | C14—C15—C16—C11 | 0.5 (4) |
N2—C4—C5—C17 | 179.1 (2) | N1—C5—C17—C22 | −40.5 (3) |
C11—C4—C5—C17 | 0.4 (4) | C4—C5—C17—C22 | 140.8 (3) |
C1—C2—C6—C7 | 1.5 (3) | N1—C5—C17—C18 | 137.8 (2) |
C3—C2—C6—C7 | −174.4 (2) | C4—C5—C17—C18 | −41.0 (4) |
C2—C6—C7—C8 | −0.7 (4) | C22—C17—C18—C19 | 0.4 (3) |
C6—C7—C8—C9 | −0.3 (4) | C5—C17—C18—C19 | −178.0 (2) |
C6—C7—C8—C10 | −180.0 (2) | C17—C18—C19—C20 | 0.8 (4) |
C2—C1—C9—C8 | 0.3 (4) | C23—O1—C20—C21 | 23.1 (4) |
C7—C8—C9—C1 | 0.5 (4) | C23—O1—C20—C19 | −157.8 (3) |
C10—C8—C9—C1 | −179.8 (2) | C18—C19—C20—O1 | 179.4 (2) |
C5—C4—C11—C16 | −41.6 (3) | C18—C19—C20—C21 | −1.5 (4) |
N2—C4—C11—C16 | 139.9 (2) | O1—C20—C21—C22 | −179.9 (2) |
C5—C4—C11—C12 | 138.3 (2) | C19—C20—C21—C22 | 1.1 (4) |
N2—C4—C11—C12 | −40.2 (3) | C20—C21—C22—C17 | 0.1 (4) |
C16—C11—C12—C13 | −0.3 (4) | C18—C17—C22—C21 | −0.8 (3) |
C4—C11—C12—C13 | 179.7 (2) | C5—C17—C22—C21 | 177.6 (2) |